I read alright, mostly sailing magazines and submarine drawings these days though. I don't have much time for blowhards. All the Gozzards I've seen look pretty similar. You sound pretty familiar, too. But like I always say, what the heck do I know?
To get back on topic, (or maybe just to get on it, since I admit I haven't so far
) the elephant in the room is risk tolerance. Some people have it, most don't. Most people cannot stand the concept of an insecure financial future. They would never consider going cruising without insurance for themselves or for their boat, and they certainly wouldn't do it without some kind of nest egg/pension fund/cottage on the bluff waiting for their comfortable retirement. They dream of cruising long distance and may even do as Jeff H suggested, short duration trips, hopping up and down the coast, maybe participate in a Newport-Bermuda every once in awhile or something similar, but they never manage to cut the ties to shore - there's always the kid's college to think about, or the needy mother-in-law, always something, just gotta make it to 30 years for a pension and retirement medical benefits ... if they just hold on for a couple more years, everything will be perfect. Next thing they know, they're in their 60's and ocean voyaging away from the luxuries to which they've become accustomed doesn't seem so enticing. The wife needs knee surgery, he's got a bad back, and the boats been on stands in their yard for two years.
I bought my boat from that guy.
I'm in my mid-thirties, married, one boy aged 8 1/2. I make pretty good money as a technical program manager, and my wife is a teacher. I'm coming up on ten years with my company, and the stock in my 401K has doubled a couple of times since I've been investing in it. The bank, my wife and I own a small house. My cash savings isn't worth mentioning at this point. If I leave my company now, I will give up most of my pension benefits and most of the investment growth in my 401K (since most of it comes from employer matching contributions.)
We're going cruising.
We've got a plan (now about 2/5 of the way through on a projected 5 year span) and we're working to it. The ten year milestone seems to be convenient for planning, as my student loans and all other consumer debt aside from my mortgage will be paid off by then. We own the boat, the tools and most of the necessary and sundry equipment already. We're getting the boat and ourselves ready and could go sooner if circumstances required (shipbuilding is a notoriously uncertain career, particularly in this era of constant downsizing.)
Will we have health insurance? Maybe not. Boat insurance? Probably not. A cruising kitty capable of providing 50K a year in income from investment return alone? No way. But we're young, skilled, intelligent, and willing to work. Like the young nurse who commented easrlier in the thread, we have portable skills. More importantly, we have confidence in our ability to make money, one way or another, along the way. We are risk tolerant, partly becasue we are young, but also inherently. With some work and effort, and a bit of luck, this will get us cruising before we're 40.
After all, what's the worst that can happen, that we've got to come back and get real jobs? (OK, not the worst, but disability, illness & injury can strike anyone, anywhere, anytime. Might as well get some cruising in before that happens.)